Synthesis of a Stable Arenesulfenic Acid Bearing a Bowl‐Shaped Macrobicyclic Cyclophane Skeleton

Abstract

A wealth of highly selective reactions may become accessible thanks to the approach described herein: A reactive functional group is placed on the inside of a bowl-shaped molecular skeleton; in this way, for example, dimerizations can be prevented, but reactions with added small molecules remain possible. The sulfenic acid 1 obtained from the corresponding S-butyl sulfoxide by pyrolysis is stable both in the solid state and in solution, and reacts smoothly with methyl propiolate and butanethiol.